It’s Hard for a Guy to Wear Women’s Clothes in Prison

When he saw the lights flashing behind him Ron knew he was in trouble. He knew it was a cop and that meant he was going to get pulled over and since he was a little bit high and there was pot in the car that meant he was going to get arrested. Since he had been arrested before on the same charge that meant he was going to end up in jail. For a guy like Ron, it’s not a good thing when he goes to jail. He’s kind of effeminate with curly, womanly blonde hair and a slim body that would remind many of a teenage girl. He’s the perfect victim for a burly prisoner to fuck some ass and not feel all that gay while doing it.

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The cop pulled him over and of course, he smelled the pot when the window rolled down. That’s why he asked Ron to kindly step out of the car and wait with his hands cuffed while he searched for evidence of marijuana possession. Not surprisingly he found a bag under Ron’s seat and when he held it up and asked if it was Ron’s the only thing he could do was hang his head and mutter that yes, he was the proud owner of that bag of pot. That earned him a trip to the squad car and his car a trip to the impound lot where he would have to pay a fortune to get it out when he was released from jail (who knew how long that would considering this was a multiple offence type of situation).

All the way down to the station Ron was pleading with the officer to let him go. “Please officer, I can’t go to prison. Look at me. Can you imagine what they’ll do to me?”

The officer did indeed look at Ron and all he could do was smile because he knew exactly what would happen. As soon as the feminine young man was placed in a cell his roommate would fuck him. It probably wouldn’t take more than 30 minutes, maybe shorter if the guard cleared out long enough. The officer actually thought it would be the perfect punishment for Ron. If there’s anything that will scare a man enough to keep him out of prison it’s the thought of being butt fucked by some dude who’s big enough to completely manhandle you anytime he wants.

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That’s why when he brought Ron to jail he made him dress in women’s clothing. He just couldn’t find any more prison outfits in the supply area so all he could come up with was a pink bra top and a short blue skirt. Ron was distressed when he saw them because he knew what that meant. He didn’t really stand a chance of not getting prison fucked when he was in his street clothes or the prison outfit but if he walked into the cell wearing women’s clothing he would be smart to just get on his knees and open his mouth so it could be fucked hard because that’s how it would be used.


The officer chuckled as Ron, humiliated, pulled on the bra and the short skirt. He was embarrassed but deep down inside, in a place where he rarely allowed himself to go he actually felt aroused. Because of his feminine nature, he had always been called a fag and teased for being girly. It happened to him from elementary school all the way through college. The older he got the less harsh they were but they never completely stopped because he was such an easy target. All of that teasing eventually had an effect on the young blonde and he harboured feelings of femininity deep inside. It went beyond merely looking like a woman; he wanted to feel and be like a woman too.

That’s part of why Ron smoked pot so much. It was a great way to make the feelings disappear, to bury them deep down inside. When he was high he wasn’t really thinking about anything other than how great it felt to be high. When he wasn’t high he was thinking about how great it would be to be a crossdresser or a sissy. He could wear women’s clothing and makeup and find men to treat him like a woman. He would let them bend him over and fuck his ass and fill him with cum. He would be their bitch and they would reward him with all the sex he could handle. Ron rarely admitted that those feelings turned him on but they did.

The only problem with his current situation is that his cellmate was not going to treat him like a woman. He was going to treat Ron like a crossdresser, a man in women’s clothing that’s a freak and needs to be fucked to feel properly ashamed of dressing and looking so slutty. When Ron walked into the cell he wasn’t at all surprised to find the man in the orange jumpsuit leap from his bed with interest in his eyes. He knew fresh meat when he saw it and this young and tasty piece of ass coming towards him was definitely a hot and fresh fuck. He was going to ram his big cock into the hot little bitch and there was nothing Ron could do about it.

Ron the sissy crossdresser was feeling a little bit romantic when he walked into the cell. He wanted to see if he could seduce the prisoner and convince him to be gentle. If he thought Ron was very womanly perhaps he wouldn’t hurt his asshole when he fucked it with what was bound to be a big cock. Unfortunately for the cute, feminine blonde crossdressing boy his cell buddy was in prison for rape so he wasn’t exactly known for his patience and understanding with women.

Before the prisoner could say anything Ron jumped in, “They’re getting a new uniform for me tomorrow and this was the only thing they had in the supply room. You have to promise me you’re not going to tell anyone that you saw me dressed as a woman. It would be terribly embarrassing and I know they’d all treat me like a fag.”

“You sure look like a fag. You look like a faggot crossdresser and I think I want to kiss you. Do you want to give me a kiss pretty girl?” the prisoner said menacingly.

Ron didn’t know what to do. If he gave in to the kiss he would probably be fucked a little more gently by his cellmate. At least there was a chance of it if the man felt some romantic attachment to him. Thinking that’s what would happen he decided to suck on the burly man’s tongue.


“Yes, I’d love to give you a kiss,” he said with the most feminine voice he could manage.

He was really playing the part now and he was enjoying it. He didn’t want to admit it to himself but he really liked the idea of being a woman for this criminal. Maybe going to jail was going to be the best thing for his sex life. Maybe the real Ron was going to come out and make his presence known as a sissy slut crossdresser that likes man cock above anything else. Only a kiss would tell him for sure.

When he felt the thick, sandpapery tongue of his cellmate slide into his mouth Ron’s cock jumped. He was a sissy slut and at that moment he knew it to be true for the first time. Suddenly he was thrilled to be in prison, at least a little bit. He would be able to explore the sexual desires that had been resting inside him for years but that he had always denied. At least that’s what he thought.

“You kiss good sissy boy, real good. I love the way your mouth tastes and now I want you to experience how my cock tastes. Get on your knees and give me head sissy slut.”

He was getting a little bit rough and demanding now but it’s not like Ron had any choice. He was locked in a jail cell with this thug wearing women’s clothing and his best bet was to go along with it. At least if he did that he wasn’t likely to end up beaten and bloody.

“Mmmmm, you are a good crossdressing cocksucker, aren’t you little girl? You give a damn good head and I’m going to love being your cellmate for a long time. I hope they convict you for life because I could sure use a blowjob queen like you in my life for the next thirty years. I’d even come back to visit you after I get out sissy slut.”

As degrading as he was being Ron couldn’t help but get aroused. His hand found his cock as he was sucking the prisoner’s long dick and he was rock hard. He was throbbing as he posed on his knees and sucked his dick. It was the oddest thing to come to the realization that he was a sissy slut but there was no doubt in his mind it was the case. He was meant to be a cocksucker and he was just proving it to be true.

“It’s time to fuck your ass sissy boy. Have you been fucked before?”

“No sir,” Ron said, looking up at him meekly from his position on the floor.

“Well, then this is probably going to hurt because I’m not known for being gentle. I like my bitches to be tight and we both know you’re going to be tight as a drum. That’s how virgins work!”


He put Ron on his stomach on the bed and fingered his asshole, working some spit in there and trying to loosen him up. He didn’t try too hard though because he didn’t really give a damn. He just wants to fuck some tight sissy ass and if Ron doesn’t like it then that’s too bad because he’s the only sissy around.

And you can bet that Ron didn’t like it. He was making all kinds of noise as his asshole was pumped by the hard dick and most of it was pleading and begging for the anal fucking to stop.

“Please, it hurts like hell. Please, pull out your cock! You’re hurting me!” he screamed in genuine agony.

“Take it bitch. You’re going to have to learn to like getting fucked up the ass because as long as you’re my cellmate I’m going to fuck you like this. You’ll be my little sissy slut fuck hole until I tell you otherwise.”

The fucking continued unabated but Ron just couldn’t stop talking because it hurt too badly. It was a pain worse than almost anything he had ever experienced and it wasn’t going to end until he had a sticky load of cum dripping from his asshole.

“You’re killing my asshole! You’re tearing me open! Please just be gentle!”

The prisoner forced his tongue down Ron’s throat because he wanted to kiss his sissy slut. He loved to have his tongue sucked while he was doing some fucking and even though Ron was in pain he obliged. He sucked the prisoner’s tongue as a good slut should.

Up until the end, Ron was moaning about how much it hurt. He had never been fucked like that but it was just the beginning for the new prisoner. His lover fucked him hard doggy style and then pulled out and shot his hot load all over Ron’s soft back. It was the first of many hot fucks for Ron as he stayed in that cell for two years serving a sentence for repeat drug offenses. He got fucked almost every night and he gave a whole lot of blowjobs, some to other prisoners that his lover had loaned him out to. When he left the prison he was a changed man, a sissy slut made to pleasure cock and nothing more. He embraced his role wholeheartedly and welcomed that change in his life.

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